This research examines the intergenerational consequences of family disruption. Specifically, we analyze the effect of living with a single parent on (1) educational attainment, (2) "inactivity," defined as not working and not attending school, (3) family formation, e.g., marriage, fertility, and divorce, (4) psychological well-being, and (5) family relationships during adulthood. Three alternative, but in some ways, complementary hypotheses are tested: (1) the "economic deprivation hypothesis," which argues that lower attainment is due to a lack of parental investment, (2) the "socialization hypothesis," which argues that lower attainment is due to differences in parental values or lack of parental control, and (3) the "neighborhood hypothesis," which argues that lower attainment is due to social isolation and lack of employment opportunity. The data include the National Longitudinal Survey of Youth (NLSY), the Panel Study of Income dynamics (PSID-1985 wave), the High School and Beyond Survey (HSB), and the National Survey of Families and Households (NSFH). Each of these surveys has one of more features that make it uniquely attractive for studying intergenerational relationships. The analyses are based on (1) OLS and logit models, used to estimate the effect of background variables on high school completion, psychological well-being, role performance and family relationships in adulthood, (2) event- history models, used to examine the effect of background variables on rates of school interruption, inactivity, marriage, fertility, and divorce, and (3) fixed-effects models, used to control for unobserved heterogeneity in examining the effect of CHANGES in family structure on CHANGES in the behavior of offspring.